#26 JooBee's newsletter

TL;DR

🪑 HR, you have a seat at the table – are you just going to sit there?

🔓 What’s in a mentor? Value unlock – see for yourself!

🎂 Fancy a Doodle Party? Join me in celebrating our 1st birthday! 

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HR, you have a seat at the table—are you just going to sit there?

There’s no shortage of advice on how to secure a seat at the table, and unlike in the past, today’s founders see value in having an HR leader around. But here’s the million-dollar question: once you’ve got that seat, how to avoid just being the one there to hold the menu?

🖼️Picture this: You’re at your leadership offsite and you find yourself seated right next to the founder at the dinner table at the end of the day. As an HR leader, what’s the conversation starter? If you were me earlier in my career, it would be one of two topics: something work-related (like the latest people challenges) or something non-work-related (from binge-worthy Netflix shows to their kid's latest antics).

Provided you’ve been in this scenario, have your conversations ever drifted to your founder’s concerns about your latest channel partner, new legislation affecting your revenue, or the latest insights on product-led customer success methodologies? Mine never did. I’m not suggesting that your founder come to you to solve their GTM or product strategy problems, but the type of conversations they naturally and organically have with you can reveal how they see you or your role.

A seat at the corner of the table

I remember being at a dinner table during an exec offsite, where every leader was casually discussing the state of the business—product and sales were diving into customer behaviour shifts, tech was buzzing about industry trends, and so on. As HR, we’re always keen to have a seat at the table. Even though this might be just the dinner table, the dynamic is the same at the executive table.

I often found myself only chiming in when the topic was people or HR challenges. When the conversation shifted to market growth or sales pipeline conversion, I felt like a 👀spectator at a tennis match—eyes glazed over, occasionally clapping. And let’s be honest, other executives probably felt the same when I was discussing People-related issues.

I want to own the table and be an equal peer

Truth be told, I navigated half my career as an HR leader without fully diving into the business's nitty-gritty…and I could have probably kept doing that just fine. I knew I was a capable Specialist HR Leader who delivered results quickly and effectively. I could have stayed within the safe confines of my HR expertise. But I know deep down that I would have never truly fit in beyond being viewed as a valued high-performing employee. In other words, even though I had a seat at the table, I still felt like I was peering through a looking glass.

My mentor at that time told me (thank you Alan Cairns!):

Taking this advice to heart, I began immersing myself in everything (and continue to do so until today) —from financials and commercials (oh, the joy of MRR, LTV, CAC, SOM, TAM - no, it is not Thai papaya salad!😅) to understanding the revenue value chain, funding, market forces, and even sitting in on customer calls with our customer success team.

Broadening my perspective

As I write this edition of the newsletter, I’m reflecting on a recent coaching session with a founder. We ended up discussing competitive pricing for his product, strategies to convert Freemium customers into paying ones, and his marketing campaign for Q4. Why am I sharing this with you?

Yes, broadening my perspective has transformed how I prioritise and strategise HR work better, allowing me to provide my team with a clearer sense of the “why” behind our actions. More importantly, I’m no longer peering through a glass but actively participating in conversations as an equal. As a result, my input on people-related matters carries a much greater impact.

From Specialist HR Leader to Strategic HR Leader

In my research for the STEP UP Strategic HR Leadership bootcamp, I asked many HR leaders about their biggest business challenges. The common themes were (and not limited to):

• We don’t have the right leaders—our people are struggling with priorities.

• We don’t have the right organisational structure—our leaders aren’t building the right teams.

• We don’t have career progression—our business is losing talent.

• We don’t have a feedback culture—our business is struggling with performance.

• We’re not holding people accountable—our managers are too ‘nice.’

These responses reveal a crucial point: we, as HR leaders, are often looking through the HR lens, operating as Specialist HR Leaders.

A Strategic HR Leader, however, is a Business Leader who understands core business challenges. In developing my bootcamp, I identified three key shifts for evolving into a Strategic HR Leader: Lens, Level, and Length.

I’m afraid I can’t cover everything in this newsletter, but I do have a little 🎁gift for you: a cheat sheet from my upcoming STEP UP Bootcamp to develop HR leaders to be more strategic! This one-pager is designed to help you broaden your business perspective and gain a deeper understanding of the challenges that keep your founders up at night. Did I mention it is only one-page?! As you know by now, brevity and straight-to-the-point, actionable tools are my speciality, and this cheat sheet is no exception. Use it as a quick yet powerful tool to kickstart your journey in becoming more attuned to the strategic aspects of your company.

What’s in a mentor? Value unlock – see for yourself!

Did you know that 76% of people think mentors are crucial, yet only 37% actually have one? For me, mentorship has been transformative in my journey to becoming a Strategic HR Leader, particularly in helping to deepen my financial, commercial and industry knowledge.

So, I’d like to share how my mentors have shaped my journey and inspire you to embrace mentorship in your own path to strategic leadership.

💰 Understanding business finance & commercials

To truly understand the financial pulse of the business, I turned to my finance leaders (wouldn’t you be surprised if I said something else?!😅). Benjamin Smith was my hero; he patiently walked me through financial statements, answered my questions and made EBITDA feel less like a medieval torture device. And Ed Goldfinger? His one-page visual on our business commercial levers (covering everything from customer acquisition to churn with a 3-year financial forecast), was nothing short of a work of art. These insights gave me a solid grasp on how our business metrics impact our financials.

🔁 Navigating the business operating model

Nick Walker (former Global Head of Delivery) and Claire Donald (former Director of Agile Delivery) generously shared their time to help me understand how various business operating models—from product development to realising customer value—can significantly impact our efficiency. This knowledge has directly informed many of my HR team’s initiatives from workforce planning to performance management. Claire, in particular, was instrumental in helping me shape my HR team so that we can operate with agile practices and adopt a product development mindset.

🎁 Unpacking product management

Product management is a cornerstone of business success, and to get a handle on it I engaged with our Product Leaders— Christian Miccio, Lidia Oyslyansky, Mark Tsirekas and Nancy Evbuomwan. Their expertise helped me appreciate the product life cycle—from ideation to market launch—and how HR can align its strategies with product goals to drive success.

📈 Diving into investment knowledge

To expand my understanding of investment, I joined a VC last year as part of my personal growth. Leaning on former VC colleagues Stephen Millard and Chris Tottman, I gained valuable insights into funding rounds, investor expectations, and market trends. This deepened my strategic perspective on how investments fuel business growth and how HR supports these financial objectives.

♠️ Embracing industry expertise

My background was in marketplace and B2C, so when I joined the iGaming industry, I was completely unfamiliar with the field. I turned to reverse mentoring with James Heard, our business analyst (now Head of Strategy). His expertise was invaluable, and he dedicated an hour every Friday morning to mentor me for over 6 months. Soon, 3 other SLT members joined in as many of us were new to the industry. Thanks, James! This experience showed me that great mentors aren’t always senior or from your immediate field—they can come from unexpected places.

Broaden your perspective with cross-functional mentors

So, I encourage you to broaden your perspective and seek out mentorship. Embrace the opportunity to learn from diverse sources—whether they’re from different levels, departments, or even industries. Mentorship can unlock new insights, enhance your strategic impact, and transform your approach to HR leadership. Don’t wait for the perfect moment—reach out, engage, and let the journey of mentorship elevate your strategic leadership!

Fancy a Doodle Party? Join me in celebrating our 1st birthday! 

Fun fact: You could’ve subscribed back in 2021, but the first issue didn’t go out until 25 September 2023! 😅 Huge thanks to the 286 early subscribers for your patience!

It took time because I wanted my newsletter to deliver real value for you. 

So, when this newsletter finally launched, my mission was clear: to give you practical, actionable advice on people and organisation challenges for scaling your start-up.

And guess what? We’re now celebrating the first birthday of the newsletter! 🎉

I’d like to invite you to make some memories and celebrate this milestone in true 21st-century fashion—by doodling asynchronously across multiple time zones and continents! 🌍

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